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The solubility of tetracosane in propane, butane, and pentane Godard, Hugh Phillips 1937

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T H E S O L U B I L I T Y O P T E T R A C O S A I ' T E I I PROPA3QL BUTANE. A N D P E N T A N E , A THESIS SUBMITTED FOR THE DEGREE OP MASTER OP APPLIED SCIENCE. HUGH P. GODARD DEPARTMENT OP CHEMICAL ENGINEERING THE UNIVERSITY OP BRITISH COLUMBIA 1937 THE SOLUBILITY OF TETRACOSANE PROPANE. BUTANE, AM) PENTANE. I. INTRODUCTION 1 I I . PREPARATION OE TETRAC0SAKE i . Synthesis 3 i x o 3?\ix* xi* x G ct*fc x oxx«•« • • « * » « « « « » * * * * * e e 4 I I I . EXPERIMENTAL PROCEDURE i i . Introduction of fetracosane..... 6 i i i . Introduction of Propane, Butane. 6 i v . Introduction of Pentane......... 7 v. Bulb Volumes.................... 8 T i . Freezing Points 8 IV. APPARATUS Pig, ... Propane Apparatus............... 2 i i i . Pentane Apparatus.... 3 i v . Freezing Point Apparatus. 4 V. RESULTS Page i . Propane - Tetracosane........... 12 i i . Butane - Tetracosane. 13 l i i . Pentane - Tetracosane..... 14 VI. CORRECTION OE RESULTS. 15 VII. TREATMENT OE CORRECTED RESULTS 16 VIII. CORRECTED RESULTS i . Propane - Tetracosane........... 18 i i . Butane - Tetracosane 19 i i i . Pentane - Tetracosane... 20 IX. VAPOR CORRECTIONS. 21 Graphs PROPANE TETRAC6SANE I I . BUTANE TETRACOSANE I I I . PENTANE TETRACOSANE IV. LOG N vs l/T THE SOLUBILITY OP TETRACOSANE IN PROPANE. BUTANE, AND PENTANE . I. ^ INTRODUCTION L a s t y e a r , Dr. W.P. Seyer, of t h e Department of I n d u s t r i a l C h e m i s t r y a t t h e U n i v e r s i t y of B r i t i s h Columbia, d e c i d e d t o i n i t i a t e a s e r i e s of s t u d i e s t o p r o v i d e q u a n t i t a t i v e d a t a on t h e m utual s o l u b i l i t i e s of h y d r o c a r b o n s . In t h e f i r s t of t h e s e r e s e a r c h e s , Seyer and F o r d y e e 1 d e t e r m i n e d t h e s o l u b i l i t y r e l a t i o n s e x i s t i n g between D o t r i a c o n t a n e ( C^gHgg ) and Propane and Butane. T h i s p r e s e n t i n v e s t i g a t i o n i s a c o n t i n u a t i o n o f t h e i r work, and p r o v i d e s s o l u b i l i t y d a t a f o r t h e p a r a f f i n h y d r o c a r b o n T e t r a c o s a n e ( C 2 4 H 5 Q ) i n the s o l v e n t s Propane, Butane, and Pentane. C o n c u r r e n t w i t h t h i s work, a number of o t h e r r e s e a r c h e r s i n t h e same l a b o r a t o r y a r e i n v e s t -i g a t i n g t h e s o l u b i l i t i e s of d o t r i a c o n t a n e i n benzene, hexane, oc t a n e , decane, and dodecane. The r e s u l t s o b t a i n e d w i l l be a l s o u s e d t o c h e c k the- s o l u b i l i t y e q u a t i o n of J.H. H i l d e b r a n d 2 The p r i n c i p a l o b j e c t i n p r e p a r i n g a c o m p i l a t i o n of s o l u b i l i t y d a t a f r o m t h e p o i n t of v i e w of the advancement of c h e m i s t r y , i s t o f u r n i s h m a t e r i a l f o r t h e o r i g i n a t i o n and v e r i f i c a t i o n o f t h e t h e o r i e s of s o l u t i o n s . As l i t t l e i s known q u a n t a t i v e l y r e g a r d i n g t h e s o l u b i l i t i e s of t h e h y d r o c a r b o n s , t h e d a t a s u p p l i e d by t h e s e i n v e s t i g a t i o n s w i l l s u p p l y t h i s want, f e l t most, perhaps, by t h e p e t r o l e u m i n d u s t r y . Of t h e v a r i o u s p r o p e r t i e s which d e t e r m i n e t h e use o f compounds i n a c h e m i c a l way, t h e s o l u b i l i t y i s of f i r s t (2) importance. Therefore s o l u b i l i t y data are perhaps of even greater interest from a pr a c t i c a l , than from a theoretical point of view. The need of the petroleum industry for data of this * sort has arisen through the introduction of solvent extraction to supplement older d i s t i l l a t i o n refining methods. Recent developments i n automotive and aviation engines i n the way of increased engine speeds, pressures, and temperatures showed that lubricants from even the highest quality crudes were lacking i n s t a b i l i t y and more e f f i c i e n t refining methods were- sought. Examples of solvent extraction processes are the Duo-Sol process of the Standard O i l Co.? and the Triton process of the Union O i l Co. ; although there are many others. The most important increa.se i n demand for chemicals during recent years i n petroleum refining has been brought about by the widespread adoption of solvent de-waxing, and solvent extraction processes employed i n the manufacture of lubricating o i l s . It i s estimated that the work of i n s t a l l a t i o n of such processes i n the industry i s only about one half completed, in 1936 there were some 4,800,000 gallons of 5 organic solvents used by the industry. With more basic knowledge available, as the theory of solutions of hydrocarbons i s c l a r i f i e d by these investig-ations and others, the petroleum refiner should be much better equipped to tackle his solvent extraction problems than he i s today, and we may expect more e f f i c i e n t methods (3) and better products, which are rapidly becoming a necessity for modern requirements. PREPARATION OF TETRACOSANE 1. Synthesis The hydrocarbon tetracosane was synthesized from CP. la u r y l alcohol, supplied by the Eastman Kodak Co., after the method of K r a f f t 6 , employing the 'Wurtz-Fittig reaction. Hydrogen Iodide, generated by the action of water on an intimate mixture of phosphorous and iodine, i n the apparatus shown i n figure 1, was led into the lau r y l alcohol which was melted by immersing the fl a s k i n warm water. The materials used were calculated on the basis of one and one half times the theoretical amount of HI required, this being done to allow for 1eaks, and gas not absorbed by the reaction, as well as an i n i t i a l portion of gas which was not used. As the reaction proceeded the alcokol turned a dark brown color and the water produced by the reaction collected i n the bottom of the flask. The iodide proved to be an o i l y l i q u i d with low freezing point, so p u r i f i c a t i o n by c r y s t a l l i z a t i o n was rejected i n favor of low pressure r e c t i f i c a t i o n . The iodide was d i s t i l l e d twice under a pressure of 9 ma, the observed temperature being 140 U. The product was a clear viscous l i q u i d with a s l i g h t l y pinkish tinge. Small fractions above and below the temperature noted were rejected. The iodide was transferred to a 500 cc round-bottom flask and just covered wi th ether to modify the succeeding reaction with sodium. A 10% excess of the theoretical amount 14) of sodium necessary was drawn into fine wire and added to the iodide, and the contents of the f l a s k refluxed for three hours. After a time the "blue color of Nal appeared, showing the reaction to be i n progress, The ether was then d i s t i l l e d off and the mixture refluxed for two hours under a temperature of 150 u. As no further reaction with the molten sodium i n the flask was observed the reaction was assumed to be complete. Alcohol (95%) was added to react with the unused sodium, the quantity being the smallest necessary. This was diluted to large volume with water to decrease the s o l u b i l i t y of the hydrocarbon i n the alcohol, which was f i l t e r e d to obtain the tetracosane thrown out of solution. The aal dissolved i n the alcohol, leaving the white s o l i d hydrocarbon, i i . P u r i f i c a t i o n The hydrocarbon was then purified by repeated cr y s t a l l a t i o n . jr o i l owing the method of i'ordyce using ether as a solvent resulted i n the loss of three weeks time and consider-able hydrocarbon. Crystals were obtainable only below -10. c , which temperature was hard to maintain and f i l t e r i n g was found to be d i f f i c u l t . It was also found that traces of ether were hard to remove from the hydrocarbon even on continued heating at 100 c . At ordinary temperatures when the l i m i t of s o l u b i l i t y of tetracosane in ether was reached, a layer of hydrocarbon-r i c h ether separated and no crystals could be obtained. A l l vessels used were coated with a f i l m of the paraffin, entailing some loss. A small amount of hydrocarbon was t r i e d i n benzene . 15) as a solvent but this was rejected as the tetracosane was too soluble and crystals were hard to obtain. Glacial acetic acid was f i n a l l y t r i e d as suggested by 7 ITildebrand ©,nd was founffl to be very satisfactory, s ix success-' ive crystallations from this solvent yielded a product with a melting point of 50.9 0 which value was constant for the la s t two c r y s t a l l i z a t i o n s . A search of the l i t e r a t u r e revealed the following values for tetracosane : 51,5e, 51.0y, 51 1 0. As the value obtained agrees closely i t was assumed that the tetra-cosane was s u f f i c i e n t l y pure to work with. 111. EXPERIMENTAL PROCEDURE i General The so called 'synthetic method* f i r s t used by Alexejeff about 1886, for the determination of s o l u b i l i t y was decided on as being most applicable to the present investigation. The operation consists of preparing a mixture of carefully determined amounts of solute and solvent i n a sealed bulb to prevent vaporization. The bulb i s then subjected to gradually increasing temperatures u n t i l the point of disappearance of the la s t crystal of s o l i d i s noted, when the temperature i s obser-ved. When a mixture of two compounds, rendered l i q u i d by elevation of temperature, i s gradually cooled, .a point i s reached at which one or other of the constituents w i l l separate as a s o l i d . This point represents the s o l u b i l i t y of one compound i n the other. The method involved di f f e r s p r i n c i p a l l y from that ordinarily employed for s o l u b i l i t y i n that the (6) composition of the mixture remains constant while the satur-ation temperature i s "being approached, instead of the reverse procedure. "While the results are necessarily obtained under different pressures, under ordinary conditions with pressures below 10 atmospheres no notable effect on the s o l u b i l i t y i s 11 produced. This pressure i s exceeded by only a few of the bulbs containing propane while a l l other pressures are considerably lower. i i . Introduction of Tetracosane Thick-walled bulbs of hard glass, 2 cm i n diameter were -blown and sealed to 9 cm stems of 3 mm tubing. Several s l i g h t l y larger bulbs were also found to be necessary.. The tetracosane was introduced into the weighed bulbs by means ofi a fine-drawn glass funnel, heated by a small flame. After cooling, the bulbs were again weighed to give the weight of hydrocarbon admitted. Ihen the f i n a l results had been obtained for pentane the bulbs were weighed, the paraffin removed and the bulbs weighed again, to check the hydrocarbon weight. These values were found to agree closely ; I.e. within .0005 gm. i i i . Introduction of Propane and Butane Introduction of the solvents gave r i s e to two procedures, one for the gases propane and butane with b.p. 's of -44.5 C, -0.5 C respectively, and another for the l i q u i d pentane with a b.p. of 36.0 C. The gas cylinders, supplied by The Ohio Chemical & Mfg. Co. of Cleveland , were connected to the apparatus shown i n figure 2. The bulbs, containing weighed (?) amounts of hydrocarbon, were sealed to the apparatus and their necks constricted. A i r was then pumped off to at least .001 mm by means of the mercury diffusion pump and o i l fore-pump. The whole volume was then "rinsed n with gas and re-evacuated, to be ' f i n a l l y f i l l e d with gas to a pressure of about one atmosphere. After equilibrium had been reached, pre-calculated amounts of the gaseous solvent were condensed into the bulbs by immersion i n l i q u i d a i r , and the bulbs sealed off at the constriction. The amount of solvent admitted was controlled by means of the stop-cock and by observation of the pressure drop, from which the weight of gas condensed may be calculated. After the freezing point of the mixture had been obtained the amount of gas was determined more exactly by weighing the bulb, allowing the gas to escape, and re-weighing the bulb and t i p . The neck was scratched by a f i l e Before the f i r s t weighing, and the bulbs cooled i n l i q u i d a i r before breking off the t i p . iv . Introduction of Pentane In the case of pentane, the desired amount of solvent was pipetted into the bulb, which was immersed i n l i q u i d a i r . The bulb, s t i l l i n the l i q u i d a i r , was then sealed to the apparatus shown i n figure 3 and evacuated with a motor pump. Hydrogen was then admitted, and the bulb re-evacuated and sealed off at the constriction. The purpose of the hydrogen i s to sweep out the remaining a i r and leave only a trace of gas. After the freezing point of the mixture had been obtained the bulbs were weighed and the tips broken off as i n the (8) case of propane. The pentane was then driven off by heating at 100 - 125 C for 30 minutes, after which the bulbs were cooled and rev/eighed to obtain the pentane weights. v. Bulb Volumes In order to correct the solvent weights for the buoyancy of the a i r displaced i t was necessary to know the volumes of each bulb. 'When each sealed set of bulbs had been prepared a record of the over-all length was taken. After the f i n a l measurements were completed and the hydrocarbon had been removed the lengths were again measured and the volume fuund from the weight of water necessary to f i l l the bulb s to the t i p . Prom the volume of the bulb to a known length, and from the over-all lengths and t i p bore the volume of each bulb was calculated. The volume of the vapor phase i n each bulb was found by subtracting the volume of the hydrocarbon and that of the solvent. v i . Freezing Points To determine the freezing points of the mixtures i n the bulbs, two constant temperature baths were set up as shown in figure 4. The thermometers used were graduated i n tenths and were calibrated against a standard resistance thermometer. Stem corrections were not made as the thermometers were calibrated under the same conditions as they met in use. The e l e c t r i c a l c i r c u i t employed i s of interest since i t gives unusual f 1 e x i b i l i t y of control and requires a minimum of equipment. Temperatures above 30 C could be main-tained within .10 C by the heaters alone. Pressure Trap A bsorption Tower s FIGURE 1 L aury/ A/co/no/ Manomafer Cylinder Gas Reservoir To McLeod Crciucje. To Fore Pump Bulbs 6 0 0 0 0 FIGURE Z (9) The hath was cooled u n t i l the white crystals of tetracosane appeared, upon which the temperature was slowly raised, with continuous agitation of the bulb, u n t i l the l a s t trace of hydrocarbon just disappeared. The temperature at this point was taken and the procedure repeated u n t i l three values agreed within .10 o. The point of disappearance was extremely sharp and could be obtained upon repetition to within .05 C. Supercooling to the extent of two to f i v e degrees wes observed. APPARATUS i . Figure 1 The absorption tower was packed with glass beads coated with red phosphorous. This was applied by dampening the red powder with as l i t t l e water possible and r o l l i n g the beads i n the paste. Its purpose i s to prevent any iodine vapor reaching the alcohol. The pressure trap was found to be a great improvement as i t prevented the alcohol being sucked back into the apparatus. i i . Figure 2 The apparatus shown was constructed of hard glass and supported on a frame. The two 5 l i t e r -gas reservoirs may be f i l l e d d i r e c t l y from the pressure cylinder with the rest of the apparatus isolated. They are contained i n an asbestos box provided with an e l e c t r i c fan and heater so that constant temperature may be maintained. The volume of the apparatus was obtained by noting the pressure drop for measured weights of gas. The weight of gas per mm of pressure drop was then calculated. This may best be F/asA =M=-6 To Hydrogen Tank. To Vacuum (10) i l l u s t r a t e d 'by the actual figures : Volume of Apparatus V = 1.4720 760 297 22.4 ^ 11.49 l i t e r s 54 273 4"4706 V - .9572 „760 ^  297'" ' -22.4 =. l l ; - 5 2 " 35. 273 44.06 • 11.50 l i t e r s These figures were obtained for propane at 25 <j and 760 mm. Weight Propane per,mm Pressure Drop w = 44.06 x 11.50 273 1 = ,8.3.-2 grams 22.4 * T "760 T Weight Butane per mm Pressure Drop w = 58.08 11.50 273 1 . 10.7 grams 22.4 - ± 760 T i i i . Figure 4 The heaters are 250 watt 110 vol t e l e c t r i c immersion heaters and may be regulated by placing a variable resistance i n series. As the two heater c i r c u i t s are the same only one need be described. '' With switch A thrown i n position 1 the heating element receives the f u l l 110 volts and the temperature of the bath i s rapidly elevated. In the 2 position there i s no c i r c u i t u n t i l switch B i s closed. With B i n position 1, there i s 97 ohms i n series with the element. This permits variation from 0 to 97 ohms. With B in position 2 there i s the 100 ohm l i g h t in series with the element and variation of the slide wire gives 100 to . 197 ohms. (11) iror temperatures above 30 (J i t was found that the resistance could he set in such position that the heater would just balance radiation losses to the room. Below 30 C control was less exact and cold water had to be used as well. (12) V. RESULTS l . Bulb No. 11 12 14 9 1 2 4 5 17 18 15 20 21 16 19 PROPANE #- TETRACOSANE Grams Tetra. .0576 .0707 .0921 .2230 .0736 .15 79 .3196 .3305 .8898 .9299 .9739 1.0087 1.0599 1.0407 2.0066 Grams Propane 2.2620 2.0202 1.932] 4.1114 .934^ .775$ .5979 .32444 j .440Q .2858 . 1611 .080). .0613 .034& .0651 Air Displaced. 15.56 13.49 11.75 14.98 9.01 8.48 8.33 9.19 6.78 5.44 6.10 6.67 5.18 7*44 7.30 Volume Vapor 11.59 9.95 8.33 7.12 7.00 6.60 6.88 8.20 4.87 3.75 4.56 5.22 3.71 6.03 4.61 P.P. C. 2.17 4.67 7.03 8.21 11.99 18.57 2 5»2X 30.50 34.17 37.75 42.49 45.65 46.56 48.52 48.22 (13) i i . BUTANE - TET.RAC0S ANE Bulb Grams Grams Air Volume E.P. Bo. Tetra. Butane Displaced Vapor C. 11 .0571 3.3928 13.73 8.17 -2.01 12 .0707 2.4328 12.43 8.32 3.90 14 .0921 1.5039 10.85 8.26 5.60 8 • .1477 1.2300 5.70 3.49 12.77 2 .1579 .6285 4.81 3.56 18.15 13 .1854 .6330 8.48 7.19 19.52 10 .1937 .3740 6.88 6.06 24.00 9 .2230 .3380 12.44 11.69 26.06 5 .3305 .3000 5.97 5.10 30.58 17 .8898 .3830 5.79 4.07 36.43 15 .9739 .2442 5.31 3.70 40.10 18 .9299 .1767 5.03 o ® 5 5 41.98 20 1.0087 .0959 (5«X X 4.72 45.00 21 1.0599 .0617 4.67 3.11 46.72 16 1.0407 .0599 6.89 5.45 47.02 19 2.0066 .0100 6.86 4 • 2 7 50.43 (14) i i i . PENTANE - TETRACOSANE Bulb Grams Grams Air Volume 3?«~f?« No. Tetra. Pentane Displaced Vapor c. 11 .0571 4.3766 14.43 7.22 -3.81 12 .0707 3.1855 13.64 8.42 2.37 14 .0921 2.0416 13.24 9.84 3.50 8 .1477 1.6091 5.15 2.37 11.16 2 .1579 1.0913 4.27 2.32 14.73 10 .1937 .5512 6.49 5.46 22.14 4 .3196 .6376 4.28 2.84 24.95 13 .1854 .2882 10.86 8.54 27.17 5 .3305 .4726 5 & 1 Q 4.00 27.98 17 .8898 .7500 6.41 4.06 32.43 9 .2230 . 1414 11.70 11.18 35.60 .18 0 9 2 9 0 .4690 4.53 2.59 36.50 15 .9739 .2678 5.78 4.10 41.19 20 1.0087 .1814 6.66 5.07 43.21 16 1.0407 .1399 7.24 ' 5.68 44.60 21 1.0599 .0762 5«25 3.77 46.51 19 2.0066 .0803 7.64 4.94 48.52 (15) VI. CORRECTION 03? RESULTS It i s necessary to correct the observed weight of solvent for the buoyancy of the a i r during the weighing of the sealed bulbs. The corrections, which are positive, have been calculated on the assumption that the bulbs were weighed at 21 C. At this temperature the weight of one cc of a i r i s .001220 grams. Another correction applied by Fordyee was for the amount of solvent i n the vapor phase at the saturation temp-erature. If the perfect gas law be assumed, and i f the vapor pressure relations are known, the amount of solvent in the vapor phase may be calculated. The following equations are talc en from the l i t e r a t u r e : Propane 1 2 log p = 4.375 - 1010 10 a W . T Butane 1 5 log p = 7.395 - 1225 Pentane 1 4 log p = 7.558 - 1446 lb mm T If n be the number of moles pv - nRT n - pv RT If M i s the molecular weight of the solvent and w the weight i n grams : w - Mn =r M pv R T (16) The propane vapor corrections with p expressed in atmospheres are then given by : w = 44.06 pv 82.07" T For butane, with p i n millimeters : „ w = 58.08 pv 62359 *~T~ For pentane, with p i n millimeters : w = 72.10 pv 62359 T When the corrections were calculated on this basis i t was found that i n the case of propane and butane,, several of the corrections exceeded the amount of solvent i n the bulbs indicating that a l l the solvent should be in the vapor state. On the other hand the freezing points indicate most de f i n i t e l y that this i s not the case. This suggests that the assumptions are i n v a l i d . Pressed for time, the author decided to neglect vapor corrections altogether and the data has been corrected for buoyancy only. This was done as i t appeared that as much error would be introduced by applying the ¥apor corrections as by neglecting them. The corrections have however been calculated and may be found tabulated with the other results. V I I . TREATMENT OF CORRECTED RESULTS The mole fr a c t i o n of tetracosane has been computed for each bulb.For each solvent the s o l u b i l i t y - temperature relati o n has been plotted, with mole percent as abscissa and temperature as ordinates. (18) VIII. CORRECTED RESULTS i . PROPANE - TETRACOSANE Bulb No. Buoyancy dorr. J (,'orr .Wt Propane •t 2.2810 Mol % Temp. C. 1 T ... / log Mol % 11 .0190 0.314 2.17 / /'. .003633 -.5031 12 Q0164 2.0366 0.450 4.67 .003601 -.3468 14 .0143 1.9464 0.608 7.03 .003571 -.2161 9 .0183 4.4297 0.651 8.21 .003556 -.1854 1 .0100 .9442 1.01 11.99 .003509 .0043 2 .0104 .7859 2.56 18.57 .003427 .4082 4 .0102 .6081 6.40 25.21 .003353 .8062 5 .0112 .3356 11.4 30.50 .003295 1.0569 17 .0083 .4483 20.2 34.17 .003255 1.3054 18 .0066 .2924 2 9»3 37,75 .003217 1.4669 15 .0074 .1685 43.0 42.49 .003169 1.6335 20 .0081 .0882 5.9.8 45.65 .003137 1^7767 21 .0063 .0676 67.5 46.56 .003129 1.8293 16 .0092 .0441 75.4 48.52 .003110 1.8774 19 .0089 .0740 77.9 4d.22 .003113 1.8915 (19) i i . BUTAIE - TETRACOSfflE Bulb no. Buoyancy Gorr. Gorr.Wt. Butane Mol % Temp C 1 T log Mol % 11 .0168 3.4096 .291 -2.01 .003690 -.5361 12 .0152 2.4480 .494 3.90 .003611 -.3063 14 .0132 1.5171 1.07 5.60 .003591 .0294 8 .0070 1.2370 2.00 12.77 .003500 .3010 2 .0059 .6344 4.10 18.15 .003434 ..6128 13 .0103 . .6433 4.73 19.52 .003418 .6749 10 .0084 .3824 8.0 24.00 .003367 .9031 9 .0152 .3532 9.8 26.06 • .003343 .9912 5 .0073 .3073 15.6 30.58 . .003293 1.1931 17 .0071 .3904 27.7 36.43 .003232 1.4425 15 . 0065 .2507 40.0 40.10 .003195 1.6021 18 .0061 .1828 46.7 41.98 .003175 1.6693 20 .0074 .1033 62.5 45.00 \ .003145 1.7959 21 .0057 .0674 • .003121 .003125 1.8633 1«359X 16 .0084 .0683 72.3 47.02 19 .0084 .0184 94.8 50.43 .003096 1.9768 (20) i i i . PENTANE - TETRACOSANE 3ulb No. Buoyancy Corr. Corr .7/t. Pentane Mol % Temp C 1 T Log Mol % 11 .0176 4.3942 .279 -3.81 .003714 .5544 12 .0166 3.2021 .468 2.39 .003631 -.3928 14 .0162 2.0578 .945 3.50 .003616 - .0246 8 .0063 1.6154 1.91 11.16 .003519 .2810 2 .0052 1.0965 2.97 14.73 .003476 .4728 10 .0079 .5591 6.9 22.14 .003388 .8838 4 .0052 . 6428 9.6 24.95 - .003356 .9823 13 .0132 .2934 11.9 27.17 .003331 1 .0755 5 .0063 .4789 - 12.8 27.98 .003322. 1 .1072 17 .0078 .7578 19.7 32.43 .003274 1 .2945 9 .0143 .1557 23.4 35.60 .003240 1 .3692 18 .0055 .4745 2$«5 36.50 .003231 1 .4698 15 .0071 .2749 43.1 41.19 .003182 1 .6345 20 .0081 .1895 53.1 43.21 .003162 1 .7251 16 .0088 .1487 60.0 44.60 .003148 1 .7782 21 .0064 .0826 72.1 46.51 .003129 1 .8579 19 .0093 .0896 82.7 48.32 .003112 1 .9175 (21) VAPOR CORRECTIONS The weights of solvent i n the vapor space, calculated by means of the equations given i n section VI are l i s t e d below PROPANE BUTANE PENTANE Bulb Grams Bulb Grams Bulb Grams 11 .1148 11 ,0352 11 . 0048 12 .1070 12 .0388 12 .0072 14 .0952 14 .0355 14 .0086 9 .0831 8 .0230 8 .0028 1 .1506 2 i:0227 2 .0031 2 .0997 13 .0423 10 .0097 4 «X 2X3 10 .0388 4 .0056 5 .1614 9 .0770 13 .0184 17 . 1049 5 .0390 5 .0088 18 .0884 17 .0383 17 .0102 15 . 1163 15 .0301 9 .0322 20 .1441 18 .0364 18 .0075 21 .1034 21 • 0343 15 .0146 16 .1749 16 .0596 20 .0181 19 .1501 19 .0671 16 .0211 21 .0151 19 . 0203 (22) AUTHOR'S NOTE While i t may be argued that this thesis i s too meticulous and f u l l of d e t a i l , the author experienced much loss of time over small points inr.the work and so i t was f e l t better to be over complete than too brief. It i t hoped that succeeding investigators w i l l f i n d the explanations clear and f u l l , that there time w i l l not be wasted repeating errors that might not have been explained here. BIBLIOGRAPHY 1. J. Am. Uhem. Soc. 58, 2029 (1936) 2. S o l u b i l i t y - j.H. Hiidebrand 3. French Patent. 770903 (1934) U.S. prior (1933) 4. U.S. Pat. 1, 988713 (1932) Chem. Zentralbl 11, 314, 1935. 5. Chem & Met. 44, 68 , (1937) 6. Berichte, 19, '2219 , (1886) 7. J. Am. Chem. Soc. 51, 2487 , (1929) 8. Kraff t , Ber. 19, 2219 (1886) 9. Hildebrand, J . Am. Chem. Soc. 51, 2487, (1929) 10. International C r i t i c a l Tables 11. s o l u b i l i t i e s of Inorganie & Organic Compounds A. Seidel l 12. J. Am. Chem. Soc. 55, 4339 , (1933) 13. International C r i t i c a l Tables 14. International C r i t i c a l Tables 

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